Want to Be a Great Leader? Get Comfortable with Uncertainty

“Leadership is ultimately an emotion, it’s a feeling. It feels like you’ve stepped into ambiguity.”

Caroline Webb is the CEO of Sevenshift, author of How to Have a Good Day, and a former partner at McKinsey & Company whose work focuses on helping professionals use lessons from behavioral economics to be happier, healthier, and less stressed by the demands of a busy life. She recently joined Peter Bregman, CEO of Bregman Partners and author of 18 Minutes and 4 Seconds, for a Heleo Conversation on the nature of leadership.

This conversation has been edited and condensed. To view the full conversation, click the video below.

https://www.facebook.com/heleoworld/videos/379572129074375/

Caroline: What has brought you to where you are now in terms of the work that you do with leaders?

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Peter: I started my career teaching leadership in expeditions: mountaineering, kayaking, wilderness, thirty day expeditions. So leadership to me has never been conceptual or theoretical. It’s been very practical. You’re with a bunch of people in the woods, and you’ve got to get from point A to point B safely. How do you get there and what are the challenges that you face? The leadership lessons that I taught or that I learned came out of the practical experiences that we had.

When I think about my focus in leadership now, it’s all about practical application. I’m not interested in leadership theory. I’m interested in how we close the gap between theory and action, in how we show up as leaders. I think there’s a very clear link from twenty five years ago when I was thirty years old doing this and now. How about you?

Caroline: I had a first career in public service and I noticed that people would be promoted into a managerial role because they were the best at the technical job that we were doing.

They would become a manager without any guidance on how to shift their focus from the technical thing they were amazing at doing to helping other people be at their best. So, as you might imagine, they were generally not great at their jobs. How could they be, and why should they be?

I became very interested in those who somehow managed, through personality or luck or perhaps they’d done some reading, to be just a little bit better at it. And it was fascinating to see the difference in how the teams felt around them.

“You can be smart in one way, but  there’s a different type of smart that you need if you’re going to be a great leader.”

And I was also working with the Monetary Policy Committee, the group that was setting interest rates in the UK. I saw how you had this collection of really smart people who were sniping at each other. There were factions in the group, and it was perhaps not dramatic enough to be a scandal, but it certainly was making the news.

I thought, this is fascinating. Having been previously focused on the technicalities of economics, it became much more interesting. What is it that makes someone perform at their best? And what is it that helps them help other people perform at their best? It was always in that context of knowing that you can be smart in one way, but that there’s a different type of smart that you need if you’re going to be a great leader.

So I went to McKinsey and focused on Organizational Change and Leadership and was there very focused on this question of what is it that unlocks that side of yourself, the more human side, that understands what it takes to motivate and engage someone else.

Peter: You used a word that I think is really important in the conversation around leadership. You said “human” being.

My career has been opportunistic more than strategic. I’ve just pursued the things that were interesting to me, but when I look back there were clear links. In journals I wrote when I was very young in my career, I wrote that the focus of my work was to bring humanness into the workplace.

Not even humanity, that’s the wrong word, but humanness. Who we are as people. We’re in a setting where people wear suits and try to be polite with each other, but we’re people, and how to invest that. I’m curious what you found.

Caroline: My practice at McKinsey was called “Leadership, Leadership Development, Leadership Coaching,” whether I was working with top teams or individuals or designing leadership programs. And I always felt that in some ways it was bit of a fraudulent term, because when I’m doing behavioral change work and helping people be at their best, is that leadership? I’m working with senior people, so we call it leadership, but sometimes colleagues of mine will say, “What’s your definitive theory of leadership? What are the four things that every leader must do? Or what are the seven or the ten things?” And I really struggled with it, I didn’t have a theory.

I felt that we knew quite a bit from behavioral science about how people could be at their best and what it takes to help other people be at their best. But beyond that, I saw so much difference in what allowed someone to flourish in how they were inspiring a whole body of people. You’re also very atheoretical and focused on the practical. What’s your theory?

“Too much confidence and I’m not curious anymore because I know all the answers. But curiosity without confidence, then you can’t ever take action because you’re always wondering.”

Peter: What are the top ten things you need as a leader? My answer would be, “Where?” At McKinsey, Capital One, or at GulfStream manufacturing airplanes? Because every culture is different—Bank of America, Morgan Stanley, J.P. Morgan, Chase, Goldman Sachs. I worked in all of them and every single one has a very different culture. The politics are different, the words we use are different, the way we work together is different.

Caroline: What is the common thing that underlies the work that you do, given that it is so different how you help someone being a great leader in different organizations?

Peter: I think most of the answers involve the word “and”. It’s confidence and curiosity. Too much confidence and I’m not curious anymore because I know all the answers. But curiosity without confidence, then you can’t ever take action because you’re always wondering.

So this combination: this willingness to be confident, to act, to move forward and to be curious, to be wrong. There’s this article on my mind to write titled, “How to be wrong.” People don’t know how to be wrong. And it’s really useful to know. It’s powerful leadership to know how to be wrong, to be able to say, “Huh, I missed that. I was wrong in that, and let’s pivot.”

Caroline: And to have the courage to take a step even though you can’t possibly know for sure whether it’s the right step to take.

Peter: Exactly. When I teach leadership, the very first thing I do is put people in a situation for three minutes where they have to make decisions with no instructions. Because that’s the feeling of leadership. Leadership is ultimately an emotion, it’s a feeling. It feels like you’ve stepped into ambiguity. If you’re following what other people are saying, you’re not leading.

Caroline: The essential condition of leadership is uncertainty.

Peter: That’s the essential condition. And uncertainty is a feeling. There’s a physical reaction we have to uncertainty.

Caroline: We know what’s going on in people’s brains when they’re facing uncertainty. There’s this study that was done in London which had people touching a hot panel. They didn’t know how hot it was going to be.

If they were given a bit of information about how hot it was going to be, they were better able to cope with the pain. And if they didn’t have any information, then the reaction to the pain was much much greater.

This is something that we’re managing for ourselves as leaders, we’re managing for other people as leaders. What is it that we can do to help our relationship with uncertainty be more positive and productive?

“Am I willing to feel uncertainty? Am I willing to feel shame? Am I willing to feel your rejection? If I’m willing to feel all that, then I can step powerfully into uncertainty and move towards the things that are important to me.”

Peter: Right. And it’s like any muscle. What is our tolerance for uncertainty? People have different tolerances. But that underlying thing is what I’m working on for my next book, what I call, “Emotional Courage: The Willingness to Feel.”

We talk so much about the courage to act. But this is the courage to feel. Am I willing to feel uncertainty? Am I willing to feel shame? Am I willing to feel your rejection? If I’m willing to feel all that, then I can step powerfully into uncertainty and move towards the things that are important to me.

Caroline: I’m working with a leader at the moment who has very high standards and wants his people to take enormous risks and to move really fast. One of the things that’s coming out of that is you’ve got to be willing to make mistakes. You’ve got to be okay with failure.

So, yes, have high standards but apply those high standards not just to the outcome, but what you’re able to learn. Because there’s going to be a lot of stuff that doesn’t quite work out, you’re going fast and taking risks.

Peter: That’s a beautiful way of putting it. To have high standards to what you’re going to learn. Which means high standards for failing well. Right?

Caroline: Exactly. “Fail fast” is a phrase that’s used a lot. But failing well…

Peter: I was working with a senior person who was very focused on accountability. I was coaching him around holding people accountable, and there were no changes happening in the organization the way he wanted them and we couldn’t understand why. He kept saying, “I want people coming up with new ideas, I want them thinking about new ways of doing things.”

And suddenly it hit me and I said, “We’re focused on helping you get people to be accountable, but the way you’re making people accountable is actually giving you the reverse of what you want. What you want from them is creativity.” And accountability and creativity are two different things.

Caroline: You’ve got to find the “and” in there.

Peter: And in fact, some of things you’re doing to hold people accountable are the opposite of what you should be doing if you’re trying to draw out their creativity. How do you find that “and”?

Caroline: There’s a lot of discussion about the future of work and what automation is going to mean for workplaces. I find myself talking quite a bit about the fact that leaders of the future will need to excel at the things that machines can’t do. Already true, but even more so, there’ll be a real premium on people who are able to bring out creativity, wisdom, empathy in the working environment. Because if you think about what can’t be automated—there’s an interesting work done by McKinsey, which looked really systematically, at what could be automated given current technology.

“The things that are least automatable are exactly what we’re talking about: creativity, empathy, wisdom, decision making where it isn’t black and white because it’s totally uncertain.”

They found that very few jobs can get automated completely away, but huge chunks of what everybody can do can be automated. And the things that are least automatable are exactly what we’re talking about: creativity, empathy, wisdom, decision making where it isn’t black and white because it’s totally uncertain.

You have to develop some kind of wisdom in how you go into that uncertainty and how you come through it. I find myself talking a lot about the fact that if you want to encourage that in people, you need to know a bit more behavioral science than is typical.

There was a time when leaders would learn strategy. Strategy would be the thing that would differentiate [you]. I feel that the next few decades, more and more people who are striving to be great leaders will need to understand how the human mind works.

Peter: I think that’s true. But the fail fast thing that you were talking about I think is [also] very true, because the world is changing so fast. Trite to say, but it’s true. I can have a great strategy that three minutes from now is not a very good strategy anymore. And so it almost feels like a key competence to powerful leadership is the willingness to fail over and over and over again.

You talk about how to not have that ruin your day, how to fail and then just keep going. Like, “Got that one wrong. It’s not a big deal, we have to move on.” Now if I’m failing and failing and not learning anything… That’s why, in 18 Minutes, I divide up five minutes in the morning, a minute each hour, and a five minutes in the evening. The idea is that when you finish work you’ve got to spend at least five minutes and go, “What did I learn today?” I know so few people who do this and it’s highest leverage five minutes that could possibly happen in your day. “What happened that I want to do differently? What do I want to do the same?”

People don’t take one minute. I often don’t take my five minutes to sit at the end of the day and say,”What came out of today that I want to learn from?”

Caroline: It helps to develop a ritual around it. Everyone says this is true, that it’s easier to remember to build a new habit if you have some hooks that allow you to place it in a specific part of your day. For me, it’s sitting with my husband at the end of the day and saying, “Okay, let’s review.” We do it every day, and that really helps.

Peter: I’m going to do that, that’s going to be my new ritual with my wife. I think to do it with someone else makes a big difference.

Caroline: And we have to look for the good things, as well. Sometimes it’s not such a great day and it’s really important to look for the good things because they can get competed out. Then you’ve got the peak-end effect, which means that as you remember the day, you remember the most intense moments and you remember the end.

Which means that having a review of the end that talks about the successes of the day brings up your average. Then the day remains in your memory bank as something more positive. That’s how we hack our days.